Showing metabocard for PC(P-16:0/18:2(9Z,12Z)) (BMDB0011211)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:14:33 UTC
Update Date2020-06-04 20:00:36 UTC
BMDB IDBMDB0011211
Secondary Accession Numbers
  • BMDB11211
Metabolite Identification
Common NamePC(P-16:0/18:2(9Z,12Z))
DescriptionPC(P-16:0/18:2(9Z,12Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(P-16:0/18:2(9Z,12Z)), in particular, consists of one 1Z-hexadecenyl chain to the C-1 atom, and one 9Z,12Z-octadecadienoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2-{[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazaniumHMDB
1-(1-Enyl-palmitoyl)-2-linoleoyl-GPCHMDB
1-(1-Enyl-palmitoyl)-2-linoleoyl-GPC (p-16:0/18:2)HMDB
1-(1-Enyl-palmitoyl)-2-linoleoyl-sn-glycero-3-phosphocholineHMDB
1-(1Z-Hexadecenyl)-2-linoleoyl-sn-glycero-3-phosphocholineHMDB
1-[(1Z)-Hexadecenyl]-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholineHMDB
GPC(p-16:0/18:2(9Z,12Z))HMDB
GPC(p-16:0/18:2)HMDB
PC(p-16:0/18:2)HMDB
Phosphatidylcholine(p-16:0/18:2(9Z,12Z))HMDB
Phosphatidylcholine(p-16:0/18:2)HMDB
Gpcho(16:0/18:2)HMDB
Gpcho(16:0/18:2n6)HMDB
Gpcho(16:0/18:2W6)HMDB
PC(16:0/18:2)HMDB
PC(16:0/18:2n6)HMDB
PC(16:0/18:2W6)HMDB
Phosphatidylcholine(16:0/18:2)HMDB
Phosphatidylcholine(16:0/18:2n6)HMDB
Phosphatidylcholine(16:0/18:2W6)HMDB
Gpcho(34:2)HMDB
1-(1Z-Hexadecenyl)-2-linoleoyl-GPCHMDB
1-(1Z-Hexadecenyl)-2-linoleoyl-sn-glycero-phosphatidylcholineHMDB
GPC(16:1/18:2)HMDB
GPC(34:3)HMDB
GPC(O-16:1(1Z)/18:2(9Z,12Z))HMDB
GPC(O-16:1(1Z)/18:2n6)HMDB
GPC(O-16:1(1Z)/18:2W6)HMDB
GPC(p-16:0/18:2n6)HMDB
GPC(p-16:0/18:2W6)HMDB
GPCho(16:1/18:2)HMDB
GPCho(34:3)HMDB
GPCho(O-16:1(1Z)/18:2(9Z,12Z))HMDB
GPCho(O-16:1(1Z)/18:2n6)HMDB
GPCho(O-16:1(1Z)/18:2W6)HMDB
GPCho(p-16:0/18:2(9Z,12Z))HMDB
GPCho(p-16:0/18:2n6)HMDB
GPCho(p-16:0/18:2W6)HMDB
PC(16:1/18:2)HMDB
PC(34:3)HMDB
PC(O-16:1(1Z)/18:2(9Z,12Z))HMDB
PC(O-16:1(1Z)/18:2n6)HMDB
PC(O-16:1(1Z)/18:2W6)HMDB
PC(p-16:0/18:2n6)HMDB
PC(p-16:0/18:2W6)HMDB
Phosphatidylcholine(16:1/18:2)HMDB
Phosphatidylcholine(34:3)HMDB
Phosphatidylcholine(O-16:1(1Z)/18:2(9Z,12Z))HMDB
Phosphatidylcholine(O-16:1(1Z)/18:2n6)HMDB
Phosphatidylcholine(O-16:1(1Z)/18:2W6)HMDB
Phosphatidylcholine(p-16:0/18:2n6)HMDB
Phosphatidylcholine(p-16:0/18:2W6)HMDB
Chemical FormulaC42H80NO7P
Average Molecular Weight742.0609
Monoisotopic Molecular Weight741.567240431
IUPAC Name(2-{[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC\C=C/OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C42H80NO7P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-42(44)50-41(40-49-51(45,46)48-38-36-43(3,4)5)39-47-37-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h14,16,20,22,34,37,41H,6-13,15,17-19,21,23-33,35-36,38-40H2,1-5H3/b16-14-,22-20-,37-34-/t41-/m1/s1
InChI KeyQLEHHUPUHJPURI-PWYDUFMYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acyl-glycerophosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-(1Z-alkenyl),2-acyl-glycerophosphocholines
Alternative Parents
Substituents
  • 1-(1z-alkenyl),2-acyl-glycerophosphocholine
  • Phosphocholine
  • Glycerol vinyl ether
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.86ALOGPS
logP8.67ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count39ChemAxon
Refractivity227.64 m³·mol⁻¹ChemAxon
Polarizability91.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q0-9070321300-08d712ae95e59b9a6662View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0239-3190111000-7b303a5b2aaf9addff0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0080-6090022000-a4ddd18d70a7723f4664View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0090001500-9c009bd6f71efaaa57d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ri-0090003000-a267acf5e9987aa9d036View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3090000000-f8d94604464dfd6ed30aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-a51c0c4e915a1e5c331cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000000900-a51c0c4e915a1e5c331cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0030911600-79981cdbe03514586380View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-0f2709050253a0bbab5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0900000500-f5c9ed3376723b6eca9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-1900436900-4b96be40525a33995f76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-eda6b98afc513e9474e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-0070012900-b16b6d4f37b94053e8a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4092200000-a2d40ca5e52ffda26441View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0011211
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027966
KNApSAcK IDNot Available
Chemspider ID24767486
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779386
PDB IDNot Available
ChEBI ID84557
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available